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Women's History Month
In Conversation with
CASSIE KNUTTI
A Techronicler interview with Cassie Knutti, Director of the Project Management Office, Caylent
In the complex world of cloud transformation, moving from a handful of people to a massive delivery engine requires more than just technical skill—it requires a blueprint for growth. Cassie Knutti, the Director of the Project Management Office (PMO) at Caylent, is the architect behind that very blueprint.
Over the last four years, Cassie has been instrumental in scaling Caylent’s project management organization from a team of five to more than 70 professionals. By blending Lean and Agile methodologies with a modern approach to governance, she has redefined how complex cloud initiatives are delivered. But her journey didn’t start in a boardroom; it began with a childhood fascination with an electronic typewriter and a series of high-stakes pivots from business operations to the frontlines of IT consulting.
For this Women’s History Month feature, we sat down with Cassie to discuss her “agentic” vision for the future of AI in project management, why she’s on a mission to solve the “mental load” for working mothers, and how sticking to the facts is the ultimate superpower in any negotiation.
Techronicler: Thank you for joining us, Cassie! Everyone has an origin story! What was the first piece of technology you ever broke, built, or fell in love with?
Cassie Knutti:
When I was younger, my parents had this electronic typewriter that I strangely fell in love with. I would just sit there for hours typing things out without the power even on! My favorite part was actually using the numeric keypad and I would just type in random things and pretend I was working at a bank.
Techronicler: A lot of careers look like straight lines on LinkedIn. How was yours different? Was there a pivotal moment or ‘happy accident’ that actually steered you toward your current role or niche?
Cassie Knutti:
Looking back, I think most people would see a straight line in my career progression, but there were several big risks and pivots that changed the trajectory of my career entirely.
The first course change was when I pivoted at MetLife from the Business Operations to the Lean Center of Excellence. We travelled each week for deployments, working with new businesses and stakeholders and that is really where I cut my teeth into my passion for process reengineering and consulting.
The second pivot was my realization that while I loved the lean transformation work I was doing, there was another initiative emerging around systems and automation that felt like the cherry on top. You can get a process down from months or weeks to days without touching technology, but in every instance – systems that were built decades ago would pop up. It was hearing repeated “the system” as a blocker that I realized I needed to take my biggest risk – leaving a company I had been at for 10 years to dive into the world of IT consulting. This is where I took my Lean experience and was asked to dive in and not only learn Agile but lead a SAFe program for a DoD program.
Techronicler: What is the one problem or project that is taking up 80% of your brain space this month?
Cassie Knutti:
AI, AI, and AI. Building our AI strategy for the PMO and how we embed it into the ways we work as early adopters. Being bold and figuring out what an Agentic PM looks like – being able to free up the administrative tasks of project managers and leverage it for insights to better manage risks, issues, and dependencies.
Techronicler: Many women still find themselves as the ‘Only’ (only woman, only WOC) in the room. When that happens now, how do you use that visibility to your advantage rather than letting it be a weight?
Cassie Knutti:
To be very honest, this is one of the many things I love about Caylent because our leadership including executive leadership is filled with women in the room. But even when I do find myself as the ‘only’ woman in the room, I do not ever feel that way – not that I haven’t in the past at other companies; but I can truly say that it never crosses my mind at Caylent.
Techronicler: Are women in leadership still penalized for being too direct or ‘sharp-elbowed’? Have you ever had to consciously unlearn the habit of being ‘too nice’ or ‘accommodating’ to get a project across the line?
Cassie Knutti:
Absolutely, and I think we penalize ourselves more than anyone else. My younger self would replay meetings or conversations back—was I too direct, too harsh? Today, it definitely still happens that I will replay things in my head but not nearly as much as early in my career and I think it’s about being confident in your skill and experience.
Techronicler: Tell us about a time you had to make a deeply unpopular technical decision (e.g., killing a feature, swapping a tech stack) that turned out to be the right call. How did you handle the pushback?
Cassie Knutti:
Coming from project management, we tend to operate in a sticky place with the engineering, development teams or even the client where we have to maintain the guardrails. There are probably too many examples where I have had to make the unpopular call.
Are we operating without a clear, understood architecture? Pause – how could the backlog be effective without knowing what the system should look like at the end.
Are we trying to put speed over quality by pushing a release to stay on schedule without unit testing? Definitely not – let’s figure out what possibly delayed us and maybe we need a change order for more time.
But the common vein when making those decisions are rooting the decision in facts and outcomes and presenting them to the Client or Team. The team will push back and might not like it, but if you present the issues, facts and possible outcomes – you get everyone to see the entire picture.
Techronicler: If you were given $10M to start a company today in a niche outside of your current field, what problem would you solve?
Cassie Knutti:
The problem I would solve would be to help offset the mental load of the working mother. There are too many women in the workplace all struggling with balancing their career and family – kid’s schedules (school, sports, activities, medical appointments), what’s for dinner, family events, house work, etc.
Techronicler: From your seat, how do you see the rise of AI tools changing the trajectory for women entering engineering today?
Cassie Knutti:
AI tools should help lower barriers for women by enabling younger girls to start exploring technology sooner by having a space to be coached through concepts, helping debug issues, etc. I also think because AI tools will help expedite coding, it will help accelerate careers into more leadership level roles focused on architecture, workflows, and orchestration.
Techronicler: What is the single best piece of advice you’ve ever received about negotiating—whether for salary, headcount, or project timelines?
Cassie Knutti:
Take emotions out of it and just focus on data and facts.
Techronicler: What is the one book every woman in tech should read this year?
Cassie Knutti:
Radical Candor by Kim Scott. I think what you can take from the book really goes back to how do you balance being ‘too nice’ and ‘too assertive’ in such an effective way.
Techronicler: What is a piece of ‘common wisdom’ in the tech industry that you completely disagree with?
Cassie Knutti:
Scrum Masters can be anyone on the development team. While yes that is true in theory and likely okay in an internal company project when you have a dedicated Product Owner; not when it comes to client work. You need someone consistent that is able and wants to act in a leadership role with the ability to challenge the team and the client on requirements, scope, estimations, velocity. I have found so many engineers and developers that do not have the skill or even want to drive those conversations.
Techronicler: If you could change one thing about how we interview and hire in tech to make the process more equitable, what would it be?
Cassie Knutti:
I think you have to put in your own quality gates to eliminate bias. We start with a resume screen to ensure they have the required qualifications, then move to an experience-based interview to dive into the qualifications and then lastly, we have the candidate deliver a scenario to a panel of leaders. This helps eliminate bias and focus on their ability to step into the role successfully.
Techronicler: The ‘broken rung’ (the first step up to manager) is a bigger obstacle than the glass ceiling. How are you personally helping junior women make that specific leap from individual contributor to lead?
Cassie Knutti:
Coaching and mentorship and well documented pathways to different positions. I think it is our job as leaders to pave the way, help others figure out what their path looks like and then enable opportunities to pull them in and keep them on the path.
Cassie’s career illustrates a powerful truth: the “straight line” we often see on LinkedIn is usually built on a foundation of calculated risks and the courage to challenge “the system.”
From her insistence on data-driven decision-making to her dedication to fixing the “broken rung” for junior women through documented pathways, Cassie is proof that modern leadership is about building structures that empower others to climb.
A heartfelt thank you to Cassie Knutti for sharing her insights on how to stay bold, stay curious, and—most importantly—stay rooted in the facts.
Cassie Knutti is the Director of the Project Management Office at Caylent, where she leads delivery governance and project methodologies and frameworks for complex cloud transformation initiatives. She has played a key role in scaling Caylent’s project management organization from five to more than 70 professionals in four years, building the frameworks and leadership structures needed to support rapid growth. Her background in Lean and Agile transformation enables her to create modern PMOs that combine strong governance with adaptable delivery models to drive meaningful business outcomes.